Updated and Upgraded in Chester Harbor by reputable licensed contractors and subcontractors, this three Bedroom, 2 bath Rancher is sure to be the talk of this quiet cul-d...

87-acre tract located Northwest of Chestertown.  Land tract was annexed into the town of Chestertown and is served with municipal services.  The property is zoned residen...

Cape Cod style home located just outside the heart of Chestertown! This home has updates throughout. Enter the front door & be greeted by an open floor plan. The spacious...

Located in the well established neighborhood of Byford Heights, this home features three bedrooms, two baths, making it a great family homer or investment property. The p...

WOW! An Eastern Shore completely renovated, turn-key home near beautiful historic Chestertown! Within an hours drive from the Delaware and Maryland beaches and Annapolis...

New Contructions - Ready for move in , in September 2023 This home features Luxury Vinyl Flooring throughout, White Shaker Cabinets, Granite Counters, Spacious Living Ro...

Currently being built in The Village at Chestertown! The Verona, a 2,302 square foot, three-story home, offers five bedrooms, and three and a half bathrooms and is positi...

New home, under construction in The Village at Chestertown! The Verona, a 2,302 square foot, three-story home, offers five bedrooms, and three and a half bathrooms. This ...

Come by this lovely BRAND NEW home in Historic Chestertown, available for move in in September. This home features Luxury Vinyl Flooring throughout, White Shaker Cabinet...

Will consider offers. Lovely Renovated Farm/Folk style home with Public water and sewer home in the village of Fairlee, just 10 minutes to downtown Chestertown. New elect...

This 3 bed, 2 bath rancher sets quietly on approximately .75 acres of land. This property offers plenty of room for entertainment with family and friends. The back yard i...

Waterfront and low maintenance located less than 1 mile from Historic Chestertown! The home is thoughtfully designed with an attached garage and first floor ensuite to a...

Completely renovated in 2006-2007 and loving cared for by the current owner! There is really nothing you need to do but move in. Wood floors can be found throughout thi...

Welcome to this charming colonial home nestled on a sprawling corner lot where timeless elegance meets modern comforts. With 4 bedrooms and 2.5 baths, this residence offe...

Quaint, historic home in Great Oak Landing with tons of character. Double front doors and double parlors. Randon width 18th-century floors. Sunroom and screened-in porch....

Introducing a stunning new construction waterfront home in Chestertown's prestigious waterfront community, Chester River Landing. Hands down, one of the best lots in the ...

Eastern Shore secluded waterfront home perched on the banks of the East Fork of Langford Creek offers commanding water views and encompasses 4.42 Acres and 235-feet of wa...

Introducing a stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite four-bedroom, two-and-a-half-bath home of...

Welcome to 121 Lyons Lane in Chestertown! This stunning property offers the best of both worlds, a waterfront private wooded setting on 3.5 acres AND located within walki...

Looking for an investment property that you can put your own personal touch on in the heart of Chestertown? This charming home needs some repairs but has the potential to...

Welcome to paradise! This incredible estate, situated on a bluff overlooking the Fairlee River will take your breath away. Situated in a peaceful, private setting, this m...

NEW CONSTRUCTION ON AN ACRE LOT. JUST ABOUT DONE. 3 BEDROOM 2 BATH RANCHER. STAINLESS STEEL APPLIANES WITH ISLAND IN KITCHEN. VINYL PLANKING FLOORING IN LIVING ROOM AND ...

Welcome to your perfect home! This stunning, completely renovated residence boasts an open interior with 9-foot ceilings, providing a spacious, airy, light-filled atmosph...

Perhaps the oldest home in Maryland. "Rock of Ages" as it's known on the deed and other documents. Captain John Palmer is crediting with erecting the home between 1633 an...

Lovingly maintained with many owner upgrades, this large 3 bedroom, 2 bath ranch home in Coventry Farms has lots of room for family and friends. The main level features ...

Move-in ready home in the Village at Chestertown! The Sidney is a 1,849 square foot open-concept two-story home, that features four bedrooms, and two and a half bathrooms...

New move-in ready home in The Village at Chestertown! The Paige is a 1,646 square foot two-story home that features three bedrooms, and two and a half bathrooms. You will...

The Sidney, a move-in ready 1,849 square-foot open concept two-story home, features four bedrooms, and two and a half bathrooms. A welcoming foyer with a coat closet gree...

Enjoy water views from this Eastern Shore two-story brick condo that is just a short walk from downtown Historic Chestertown parks, shops and dining. A major renovation i...

Lovely Renovated Farm/Folk style home with Public water and sewer home in the village of Fairlee, just 10 minutes to downtown Chestertown. New electric, plumbing, and dry...

Prime location plus Guest house! This beautiful historic home boasts one of the most elegant modern interiors in town. It was completely gutted, rebuilt, and expanded in ...

*PUBLIC OPEN HOUSE - Thursday, may 18th, from 4-7pm!* The CUTEST farmhouse - with so many upgrades - on one full acre!

Walk to Historic Chestertown’s restaurants, shops, waterfront & marina! Just blocks away from the University of Maryland Shore Medical Center and Washington College! One ...

This wonderfully renovated, 3 bedroom, 2 bath home is move in ready! Open concept living featuring vaulted ceilings, hardwood floors, granite counters, stainless steel a...

Clean as a whistle and ready for its new owners! This three bedroom, two bath ranch home in Chesapeake Landing has many new upgrades including new flooring, paint, and a...

Sportsmans Paradise..... 3 Bed 2.5 Bath Cape Cod nestled on 36 acres, 2nd Additional Perc in the back corner of the property. This home features Granite kitchen counters,...

Located in Kingstown Manor this 3BR, 2BA well appointed home is ready for it's new owners! 1,780 sq ft finished living space - the open floor plan includes a LR with gas ...

BUY THIS AWESOME HOME FOR LESS THAN $2,800 PER MONTH OR TRADE! SPECIAL FINANCING AVAILABLE: RATES LESS THAN 4.6% FOR THOSE WHO QUALIFY. OCCUPYING A VAST, RESIDENTIAL BLO...

Check out Chester River Landing's newest construction! This three bedroom, three and a half bath, townhouse is a spacious end unit with incredible views of the Chester Ri...

Check out Chester River Landing's newest construction! This middle unit, three bedroom, three and a half bath townhouse is spacious and has incredible views of the Cheste...

Welcome to this charming and elegant 2 bedroom, 2.5 bathroom condo nestled in a tranquil water-oriented community near the Chester River in the historic town of Chesterto...

Your dream house awaits in the most perfect location! This delightful custom built home, being offered on one of the most sought after streets in Downtown Chestertown, an...

Entering the main level through a covered slate porch, you will find a living room, a dining room, a kitchen with a breakfast area that is opened to a wonderful family ro...

Two apartment dwelling sited on 2.51 acres zoned Village offers town water/sewer with units served with separate electric meters. The large spacious open area behind th...

Two apartment dwelling sited on 2.51 acres zoned Village offers town water/sewer with units served with separate electric meters. The large spacious open area behind th...

Eastern Shore home is located in Chestertown in Queen Anne’s County and offers glimpses of the Chester River. In 2019 the kitchen underwent a complete renovation with an ...

3,932 total square feet of a immaculately maintained, clean to perfection home! These owners have managed to keep this home just about in perfect condition right down to ...

Eastern Shore home offers views of the Chester River and is just a walk away from downtown Chestertown. Lovely two-story brick condo has water views and an unbeatable loc...

Come by this lovely BRAND NEW home in Historic Chestertown, available in for move in Early Summer. This home features Luxury Vinyl Flooring throughout, White Shaker Cab...

Come by this lovely BRAND NEW home in Historic Chestertown, available in for move in by Late May 2023. This home features Luxury Vinyl Flooring throughout, White Shaker...